Manganese(I)-Catalyzed C–H Allylation of Tryptophans and Their Oligopeptides On Water DOI
Fabrice Gallou, Lutz Ackermann, Julia Struwe

et al.

Synlett, Journal Year: 2024, Volume and Issue: 35(08), P. 903 - 907

Published: Feb. 14, 2024

Abstract The manganese(I)-catalyzed allylation of the amino acid tryptophan is realized under exceedingly mild conditions using water as a sustainable and non-hazardous reaction medium, instead classical organic solvents, with great potential for green chemistry. Synthetically useful α,β-unsaturated esters can be accessed by Morita–Baylis–Hillman (MBH) adducts following fast C–H activation approach. robustness this procedure reflected kinetic analysis at different temperatures reduced catalyst loadings are employed.

Language: Английский

Electrochemical Late-Stage Functionalization DOI Creative Commons
Yulei Wang, Suman Dana, Hao Long

et al.

Chemical Reviews, Journal Year: 2023, Volume and Issue: 123(19), P. 11269 - 11335

Published: Sept. 26, 2023

Late-stage functionalization (LSF) constitutes a powerful strategy for the assembly or diversification of novel molecular entities with improved physicochemical biological activities. LSF can thus greatly accelerate development medicinally relevant compounds, crop protecting agents, and functional materials. Electrochemical synthesis has emerged as an environmentally friendly platform transformation organic compounds. Over past decade, electrochemical late-stage (eLSF) gained major momentum, which is summarized herein up to February 2023.

Language: Английский

Citations

141

Recent developments in the cleavage, functionalization, and conjugation of proteins and peptides at tyrosine residues DOI Creative Commons
Shengping Zhang, Luis M. De Leon Rodriguez, Freda F. Li

et al.

Chemical Science, Journal Year: 2023, Volume and Issue: 14(29), P. 7782 - 7817

Published: Jan. 1, 2023

Peptide and protein selective modification at tyrosine residues has become an exploding field of research as constitutes a robust alternative to lysine cysteine-targeted traditional peptide/protein protocols. This review offers comprehensive summary the latest advances in tyrosine-selective cleavage, functionalization, conjugation peptides proteins from past three years. updated overview complements extensive body work on site-selective proteins, which holds significant relevance across various disciplines, including chemical, biological, medical, material sciences.

Language: Английский

Citations

29

Diversification of pharmaceutical molecules via late-stage C(sp2)–H functionalization DOI Creative Commons
Weidong Shang, Hongbao Sun, Wei Chen

et al.

Green Synthesis and Catalysis, Journal Year: 2023, Volume and Issue: 4(2), P. 104 - 123

Published: Jan. 2, 2023

C–H late-stage functionalization has gradually become a powerful approach for the rapid optimization of lead compounds' bioactivity. Significant advances in this field have been achieved past few years, mainly, system (hetero)aryl activation owing to importance moiety pharmaceutical. In review, we described selected recent examples how developed intermolecular C(sp2)–H methodologies involving diverse techniques diversify pharmaceutical molecules late stage.

Language: Английский

Citations

24

Electrochemical synthesis of peptide aldehydes via C‒N bond cleavage of cyclic amines DOI Creative Commons

Xinyue Fang,

Yong Zeng,

Yawen Huang

et al.

Nature Communications, Journal Year: 2024, Volume and Issue: 15(1)

Published: June 18, 2024

Abstract Peptide aldehydes are crucial biomolecules essential to various biological systems, driving a continuous demand for efficient synthesis methods. Herein, we develop metal-free, facile, and biocompatible strategy direct electrochemical of unnatural peptide aldehydes. This electro-oxidative approach enabled step- atom-economical ring-opening via C‒N bond cleavage, allowing homoproline-specific diversification expansion substrate scope include amides, esters, cyclic amines sizes. The remarkable efficacy the electro-synthetic protocol set stage modification assembly linear macrocyclic peptides using concise synthetic sequence with racemization-free conditions. Moreover, combination experiments density functional theory (DFT) calculations indicates that different N -acyl groups play decisive role in reaction activity.

Language: Английский

Citations

11

The crucial role of silver(i)-salts as additives in C–H activation reactions: overall analysis of their versatility and applicability DOI Creative Commons
Renato L. Carvalho, Emilay B. T. Diogo, Simon L. Homölle

et al.

Chemical Society Reviews, Journal Year: 2023, Volume and Issue: 52(18), P. 6359 - 6378

Published: Jan. 1, 2023

This review discusses the important role of silver( i ) salts as additives in transition-metal catalyzed C–H activation, and depicts discussion about current shift towards Ag-free procedures, plausible sustainable alternatives.

Language: Английский

Citations

21

Recent Progress in Electrochemical Modification of Amino Acids and Peptides DOI

Xinyue Fang,

Yawen Huang,

Xinwei Hu

et al.

Chinese Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 44(3), P. 903 - 903

Published: Jan. 1, 2024

Language: Английский

Citations

7

Synergistic Photoredox and Electrochemical Catalysis in Organic Synthesis and Late‐Stage Functionalizations DOI

Ci‐Yang Sun,

Ting‐Jun Lin,

Yu‐Yu Chen

et al.

ChemCatChem, Journal Year: 2024, Volume and Issue: 16(14)

Published: Feb. 7, 2024

Abstract This review delves into the innovative field of interfacial photoelectrochemical (iPEC) and (PEC) catalysis, dynamic synthesis methodologies that seamlessly integrates electrochemical photoredox catalysis for efficient environmentally friendly reactions. Utilizing minute quantities photocatalysts, visible light becomes a powerful tool, generating transient excited states to catalyze spectrum reactions through single‐electron oxidation or reduction events. The categorizes recent advancements, highlighting applications in organic synthesis, late‐stage modifications, distinctive features methodology. Despite being its early stages, this synergistic approach holds great promise propelling forward, with potential large‐scale diverse functionalizations, including asymmetric bioconjugation strategies biomolecule modifications.

Language: Английский

Citations

6

Transition Metal‐Catalyzed C−H Functionalization Through Electrocatalysis DOI
Prabhat Kumar Baroliya, Mukesh Dhaker, Subir Panja

et al.

ChemSusChem, Journal Year: 2023, Volume and Issue: 16(12)

Published: March 7, 2023

Electrochemically promoted transition metal-catalyzed C-H functionalization has emerged as a promising area of research over the last few decades. However, development in this field is still at an early stage compared to traditional reactions using chemical-based oxidizing agents. Recent reports have shown increased attention on electrochemically functionalization. From standpoint sustainability, environmental friendliness, and cost effectiveness, oxidation metal catalyst offers mild, efficient, atom-economical alternative chemical oxidants. This Review discusses advances metal-electrocatalyzed past decade describes how unique features electricity enable economic sustainable way.

Language: Английский

Citations

13

The thiol-sulfoxonium ylide photo-click reaction for bioconjugation DOI Creative Commons
Chuan Wan,

Zhanfeng Hou,

Dongyan Yang

et al.

Chemical Science, Journal Year: 2022, Volume and Issue: 14(3), P. 604 - 612

Published: Dec. 3, 2022

Visible-light-mediated methods were heavily studied as a useful tool for cysteine-selective bio-conjugation; however, many current suffer from bio-incompatible reaction conditions and slow kinetics. To address these challenges, herein, we report transition metal-free thiol-sulfoxonium ylide photo-click that enables bioconjugation under bio-compatible conditions. The is highly generally finished within minutes with naturally occurring riboflavin derivatives organic photocatalysts. catalysts substrates are readily accessible bench stable have satisfactory water solubility. As proof-of-concept study, the was smoothly applied in chemo-proteomic analysis, which provides efficient tools to explore druggable content of human proteome.

Language: Английский

Citations

20

Review of electrochemical transition‐metal‐catalyzed C−H functionalization reactions DOI

Sumi Changmai,

Sabera Sultana, Anil K. Saikia

et al.

ChemistrySelect, Journal Year: 2023, Volume and Issue: 8(11)

Published: March 14, 2023

Abstract The combination of organometallic C−H activation and electro‐catalysis has emerged as a potent synthetic technique for various molecular scaffolds since it avoids the use harmful expensive chemical oxidants in stoichiometric amounts. Moreover, pre‐functionalization substrates is not required newer ways to perform metal‐catalyzed reactions are possible. Here, we have discussed eletrochemically driven acyloxylation, acetoxylation, oxygenation, acylation, amination, alkylation, halogenation, olefinations C−H/N−H annulation using transition‐metal‐catalyst such Ru, Rh, Pd, Co, Ni, Ir, Cu, Mn Au by anodic oxidation, followed reductive elimination form corresponding C−O, C−C, C−N C−X (X=Cl, Br, S etc.) bonds. This review covers recent developments transition‐metal‐catalyzed electrochemical from 2007 until 2022.

Language: Английский

Citations

12